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Love Letters

Ready to date a friend

Submit your question to Meredith here.

Q. I’m in love with my best friend. I know — so cliché. We became fast friends our freshman year of college and have spent practically every free second together since.

We’ve even earned nicknames from our friends because we’re always together. We did a joint costume for Halloween (it was really cute). We’re extremely affectionate toward one another, often holding hands or cuddling in bed while watching movies.

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I haven’t asked him out and honestly never thought I’d ever get the chance to because he’d been dating the same girl on and off for around two years. They broke up about a week ago (for perhaps the third or fourth time) and I’m really thinking about confessing my feelings to him. You know, a new year and a fresh sense of optimism.

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Of course, there’s the ever-present fear that my feelings won’t be reciprocated and I could ruin a perfect friendship. He is my best friend and was that before anything else. Is it worth being honest about the feelings I’ve developed as we’ve continued college or should I just let it go and hope for the best?

Hoping for the best

A. It’s time to ask questions and confess your feelings. You’re already cuddling in bed together; your need for this conversation shouldn’t shock him.

As we learned from so many letters, timing is a big deal, and if you’re both single — finally — you don’t want to miss your chance to find out whether this can turn into a romantic relationship. Do not wait too long or talk yourself out of disclosure. It’s scary, for sure, but so is the idea of putting this off for another year (or more).

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This fear of losing a best friend makes sense; he’s your constant companion. But if he’s a good friend, he will want you to know where you stand. Also, yes, rejection is terrible, so I get why you’re delaying this. But from my experience, missed opportunities feel worse.

Meredith

READERS RESPOND:

What’s going on is that without their helicopter parents, kids don’t know how to navigate even the simplest of situations. -ROADRUNNER-

Admit it sister, you’ve been in love with him for four years waiting for this moment. Either [expletive] or get off the pot. ASH

I had a friend like this in college. We did everything together — took me out for ice cream, took me away on his birthday, took me to a local county fair (yeah, memorable), and we both didn’t admit feelings for each other. Many years later, he admitted he should have told me how he felt about me. Did I want to smack him? Yes. Did I sort of smack myself, yes. Was there anything I could do about it? No — timing again. I was married at that time, and just when I got the divorce, HE got married to a wonderful woman who happens to also be a friend. MHOUSTON1

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If you believe friends cuddle, when you become a couple with the guy, you won’t mind him cuddling with other girls, right? I didn’t think so. JACQUISMITH

I had a really close female friend in college, my first ever and really only ever since. Definitely more of a guy who hangs around with other guys. . . . I NEVER would’ve thought of holding hands with her or “cuddling” or doing a tandem costume with her. (I’ll let you in on a little secret: It probably wasn’t “really cute” to everyone, and certainly not to his girlfriend.) Don’t do that. Hope his ex finds someone more worth her time. Best of luck! SOUTHIE777

Sigh. I feel so old. I don’t understand this at all. Back in my day, if a boy cuddled and held hands with a girl and spent every free second with her, then he was her boyfriend. If he had sex with someone else, then he was a cheating cheater. But he’s having sex with his girlfriend and being intimate (non sexually) with you. Tell him how you feel, and maybe he’ll become your boyfriend. But, just be prepared — he thinks it’s fine to cuddle and hold hands with the person he’s spending his free time with which will be . . . not you. COSMOGIRL

Column and comments are edited and reprinted from boston.com/loveletters. Send letters to meredith.goldstein@globe.com.